Sammy's Secret
by briewinchester88
Summary: Sam has always know that he was born in the wrong body. He started pursuing his true identity at the age of sixteen, carefully hiding it from his brother and father. Not only was Sam harboring this secret, he was also hiding secret feelings for his older brother. Things come to a head on the mystery spot case and Sam's secrets are revealed. / Wincest. Rated M for sexual content.


Ok, so I'm kinda nervous about this one. I've never written a fic like this before. Please be nice in your comments. Constructive criticism is welcomed. Thanks. I hope you like it.

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Dean was running around their motel room frantically, looking for his gun. Sam was waiting inside the door, impatiently. Dean was rummaging through their duffles and came across a black and purple lace bra.

He held it up and looked over at Sam and said jokingly. "Is this yours?" Sam had to hide his horror at Dean finding that so he gave his best bitch face and raised his hands.

Dean finally found his gun and they walked down the street to the diner. The whole way there, Sam was silently freaking out inside his mind. He was really nervous, jumpy, and he was starting to sweat.

Sam knew when he was a young teenager that he was drawn to women's clothing. He was captivated by the vibrant colors and the soft fabrics. He loved the way they felt on his skin, hugging him in all the right places. His most favorite pieces are the lingerie.

Oh, the many different kinds fabrics there are. Lacey ones, silky ones, a mixture of lace and silk, corsets with garter straps, leather ones, he could go on and on. He had also dabbled in wearing make-up. He was never one to go all out drag queen with the make-up, he kept it simple.

He liked to experiment with colors, but liked the warm earth tones the best. He never liked the glittery make-up; it was just too tacky for his taste. Sam liked to indulge in his fetish when Dean was going to be gone for a while.

He liked taking his time getting ready. If Dean ever found out about his 'extra-curricular activities', he would never hear the end of the girl jokes. Sam was pulled away from his thoughts by Dean nudging him in the ribs.

He shook his head. "Dude, what the hell?"

Dean gave him his serious-yet-concerned look. "Dude, where'd you go? I've tried to get your attention for ten minutes now. Are you alright?"

Sam was rubbing the spot where Dean elbowed him. "Yeah, I'm fine. I was just thinking about what to get for breakfast."

Dean was skeptical, but let it go. They walked into the diner and they took a seat in a booth at the back of the diner. The waitress came over to take their drink orders. Sam, again, got lost in his thoughts about his 'extra-curricular' activities.

Dean was watching his younger brother across the table. He had his head down, bangs covering his eyes, and he was obviously lost in his head. He tried to get his attention by snapping his fingers in front of his face.

Sam jumped at the proximity of Dean's fingers in his face. "Dude, seriously!"

Dean chuckled and leaned back in his seat. "Aw, come on Sammy. Dude, you keep checking out on me."

Sam's face flushed a deep crimson and he tried to fold deeper into himself. Dean was very worried about Sam's unusual behavior. He leaned forward and rested his forearms on the table and folded his hands. "Sam, are you sure you're alright? You're acting weirder than normal."

Sam fidgeted in his seat and was saved from answering Dean by the waitress bringing their food to the table. Sam smiled kindly at her and started eating his pancakes. Dean just stared incredulously at him and started in on his breakfast. They ate in relative silence.

Sam was the first one done and excused himself to the restroom. He exited the booth and quickly ran to the bathroom. He opened the door and went to the sink and splashed cold water on his face. He was starting to get all hot and bothered at the table, thinking about his secret life.

He was leaning on the sink counter and trying to get his breathing under control. He opened his eyes and clearly saw the tent forming in his jeans. He groaned inwardly. He really needed to get Dean away from the motel.

It's been a while since Samantha got to come out to play. He walked back out into the diner and rejoined his brother. It's getting harder and harder to keep Samantha under Dean's radar. Dean paid for breakfast and they left the diner to start their day of researching.

Sam was on edge all day and it wasn't helping that Dean kept looking at him out of the corner of his eye. Sam grit his teeth and tried to reign in his anger and annoyance. They spent the day in their motel room, Sam was on the laptop and Dean was…being Dean.

Sam got a few minutes to himself when Dean left to grab some lunch. Once the door closed, Sam sighed with relief. He leaned back in his chair and wiped his hands over his face and through his hair.

Sam was going stir crazy! He really, really needed to get Dean out of the motel tonight. How he's going to do that, he doesn't have the slightest clue. He felt his skin buzzing with pent-up sexual tension. He was about to go out of his fucking mind!

He hadn't gotten any since the last time Samantha got to come out to play and he forgot how long ago that was. He got up and started pacing the room. He was shaking violently with the need to become Samantha that he started sweating profusely. He felt hot all over and his face was flushed. He went to the bathroom and splashed cold water on his face.

He tried not to look at himself in the mirror; he'll only see _her_ behind his eyes, itching to get out. He splashed more water over his face and through his hair. His breath was coming out in pants and he _REALLY _needed to let her out.

He looked up and saw his reflection in the mirror and gulped heavily at what he saw staring back at him. He frantically backed away from the sink and his back hit the wall. His hands splayed out beside him on the wall, chest rising and falling quickly, staring at Samantha in the mirror.

He bolted out of the bathroom to get away from _her. _He never heard the roar of the engine or Dean come barreling through the door until he almost plowed him over. Luckily for Dean, he had already put the food on the table or else it would be all over him and the floor.

Dean caught Sam as he came barreling out of the bathroom. He gave his little brother a once over; chest heaving, sweating profusely, shaking, no signs of injury. What the fucking hell was going on with his little brother today?!

Dean directed Sam over to the edge of the bed and sat him down. Dean was watching Sam's behavior and sighed. "Ok, you take a nap; I'll finish up the research."

Sam looked at him and tried to stand up. "No, no i-it's ok. I can finish up the research, you eat and watch tv."

Dean placed his hand on his shoulder and sat him back down. "No, Sam, you need some sleep. I don't know what the fuck's been going on with you lately, but you're exhausted, man. Get some sleep; I'll take care of this." Sam knew there was no point in arguing, so he laid down and closed his eyes.

Dean watched as Sam fell into a fitful sleep. He sat on the edge of his own bed and wiped his face. His eyes roamed down his little brother's body and paused at the swell of Sam's ass.

He shook his head and stood up and he strode over to the table where Sam's laptop was sitting. He sat down in front of it and tried to decipher what Sam was working on.

Sam was tossing and turning on the bed, hundreds of images were flying through his head at a million miles an hour. It wasn't necessarily a bad dream per se; just that Samantha was trying to find her way out. Sam bolted upright in his bed, chest heaving and drenched in sweat.

He looked at his watch and was surprised that he slept for as long as he did. He saw movement out of the corner of his eye and looked over at Dean, sitting in front of the laptop, just staring at him.

Dean was automatically concerned at Sam's incessant tossing and turning, worried that he was having a nightmare. When Dean was sure that Sam wasn't in any kind of distress, he went back to looking at the computer screen. "You alright, Sam?"

Sam glanced at his brother, and then quickly looked away from him, hiding behind his bangs. All the images that he dreamt about came flooding back to him in an instant; making him blush a deep crimson. A light shudder ran down his spine, arousal setting in causing his jeans to tighten to the point of becoming uncomfortable.

Dean was watching him with one eyebrow raised. "Sam, I asked if you were ok."

Sam looked over at him and shook his head. "Yeah, I'm fine. I'm just, going to go take a shower." he ran past Dean and into the bathroom and slammed the door. He leaned up against it and tried to get his breathing under control.

He started the shower up and stripped down. Dean listened as the shower started up and closed the laptop. He sighed and stood up, put on his jacket, grabbed his keys, and left Sam a note. Sam stared into the mirror and he couldn't take it anymore!

"Fuck this." he said to his reflection and finally let Samantha come out to play. She grabbed her razor from her toiletries bag and stepped into the shower. She started off shaving her legs and moved on to her armpits.

She looked down at the wiry hair at the base of her cock and shaved that as well. She put her razor down and proceeded to wash her hair and body. When she finished her shower, she dried off and exited the bathroom. She saw no sign of Dean anywhere and saw a note sitting on the table.

She walked over to it, read it, and smiled. She walked over to the dresser (that they never use) and pulled out her duffle containing all her clothes and accessories. She went back to the bathroom, getting herself ready for a night on the town. She dried her hair, put in her extensions, and curled it.

Once she was satisfied, she went back into the room and picked out her outfit for the night. She rummaged through her duffle bag, looking for her favorite pair of panties. She grinned triumphantly when she found them. She dropped her towel and pulled the black and purple thong up her smooth, muscular legs.

She found the black and purple bra that Dean held in his hand just that morning and put it on. She put the fake breasts in her bra and adjusted it, making sure they were straight. She found her favorite denim mini skirt and put it on, sighing happily at the feeling of the cloth against her smooth skin.

She sorted through her shirt collection, looking for the perfect one. She finally decided on her black tank top and Dean's old Metallica t-shirt, which she cut the collar off of. Once she was dressed, she went back to the bathroom to put on her make-up. She chose an orchid colored purple, pairing it with a navy blue accent.

She used her liquid black eyeliner and made a little design at the corner of her eyes. She used a peach blush, accentuating her sharp cheek bones and spread a light pink lip gloss over her luscious lips. She put on her deodorant and stared at her reflection, trying to decide how to fix her hair.

Finally, she pulled it back and secured it with jeweled bobby pins. She grabbed her fish net stockings out of her duffle and put on her knee-length black leather boots. She finished off her ensemble with her favorite black leather jacket.

She grabbed her purse and filled it with her phone, room key, some extra cash, her knife, and gun inside. She took one last look at herself in the mirror and with a satisfied smirk, headed towards the motel room door.

Samantha was lost in her excitement of going out that she never heard the Impala pull into the parking space in front of their room. Right as soon as Samantha opened the door, she ran right into Dean. She stood frozen like a deer caught in the headlights.

She couldn't move or speak. Dean stood there, staring. He was trying to process what the fuck was going on. When he left earlier that evening, his brother was in the shower. Now, he comes back to find said brother had turned into his sister.

If he's gonna get through this conversation, he's gonna need a drink or twelve. He barreled past Sam and into the room, heading straight for his duffle bag and pulled out his flask of whiskey.

Sam closed the door and leaned against it, head down. She couldn't bear to see the look of revulsion in her brother's eyes. She had planned on telling him, she just didn't know how to start that conversation. This was definitely not how she planned on telling Dean about Samantha. Dean took a few more swigs of whiskey before he got the courage to look at Sam.

He saw her; long hair covering her pretty face. He raked his eyes over her from head to toe. He let his eyes roam slowly over her mile long, muscular legs coming out of the short, short skirt.

He could just imagine when she bent over that he could see her panties. He was starting to get hard in his jeans, staring at his brother/sister. She sure looked gorgeous. He looked even closer at her and noticed that she was wearing his old Metallica t-shirt. He smirked. "You got something you want to tell me, Samantha?"

She didn't expect shivers to run up and down her spine at her brother's voice, but she got confused at his tone of voice. He didn't sound angry, or disgusted. No. He sounded, amused? Maybe a little aroused? She looked up at him and stared into his emerald-green eyes.

She was starting to get all hot by the look of lust she saw in her brother's eyes. She started panting and fidgeting against the door. Dean felt a primal need overtake him. He wanted Sam to dress like this all the time. There was something about Sam dressing like a girl who pushed all his buttons.

When she opened her mouth to answer Dean's question, she spoke softly and looked away from her brother's eyes. "I've dressed like this since I was sixteen. It started out as little things, like wearing panties at first. Then I moved on to bras and so on. I started experimenting with make-up in college. Sam tried so hard to hide me all day, but I wanted out so bad! I needed to play, to be played with." she started playing with her hair and raised her head when she heard Dean groan.

Dean could hardly believe that he didn't notice that his brother was cross-dressing at such a young age. Which raised a question in his head, was Sam a virgin? He listened as Sam finished her story and groaned when she said she wanted to play and be played with. He watched her snap her head up and Dean locked eyes with hers.

He had to know. "Sammy I gotta know, are you a virgin?"

Sam threw her head back against the door and groaned. "Why did you have to ask me that?" she lifted her head back up and stared in his eyes. "No Dean. I'm not a virgin."

Something inside Dean snapped and he was up off the bed quicker than a jack rabbit and pressing his body into hers. He growled low in his throat. "How old were you?"

Sam gulped and pressed back against the door. "Eighteen, the week before I left for Stanford."

Dean was shocked to learn that. He reached up and cupped the side of her face. "Sammy, why didn't you tell me?"

Sam could feel tears start to gather in his eyes at the hurt he heard in his brother's voice. He looked away from Dean, but still leaned into his touch. "I was afraid that you would hate me. I was afraid that you would leave if you found out about Samantha."

Dean was surprised at how quickly Sam could switch back and forth between himself and Samantha. He stroked his thumb along Sam's cheek and smiled sadly. "Sammy, you gotta give me a little more credit than that. I'm your brother and no matter what, I could never leave you. It would've taken some getting used to, yeah, but I could never ever hate you. It's not how I'm wired."

Sam looked up at his brother, tears glistening in his eyes. "Thanks Dean, that means a lot to me."

Dean knew it was now or never. He leaned in and gently pressed his lips to hers. Sam's eyes widened in surprise as her brother's soft lips pressed against her own lip gloss covered ones.

She let her eyes fall shut as she responded to her brother's soft kiss. Dean was elated that Sam was kissing him back and that she apparently felt the same way.

He brought his other hand up and cupped her other cheek and angled her head to deepen the kiss. Sam brought her arms up and hooked them around Dean's neck and pressed her body closer to his.

Dean moaned as he felt her body press up against his. He took one of his hands and ran it down her neck, over her chest, and rested it on her thigh. He grasped the back of it and brought up around his waist. He slid his hand up higher and went under her skirt, feeling what kind of panties she was wearing.

He growled when he felt the thin straps of a thong hugging her hips. Sam moaned at the feeling of Dean's calloused hands on her smooth legs. It sent shivers down her spine and goose bumps to rise on her skin.

Dean reached down and pulled her other leg up and around his waist. Sam locked her long legs around Dean and bucked her hips up against Dean's. She moaned at the contact. Their tongues battled for dominance as Dean tangled his fingers in her long beautiful hair and tugged, causing her to moan which allowed Dean to take over the kiss.

Dean moved both of his hands back around and grabbed her ass and squeezed. Sam broke away from the kiss and gasped. "Dean! God, that feels good."

Dean trailed his mouth down her jaw, leaving little kisses and nips over to her ear. He kissed at the sensitive spot behind her ear and bit down. She moaned and bucked her hips up into Dean's again.

She managed to pull Dean's head away from her skin long enough for her to look in his eyes. "Dean, let's take this to the bed yeah?"

He wrapped his arms around her waist and carried her over to the bed. He laid her down gently and climbed on top of her and started to kiss her neck and went back up to her ear and started nibbling on her earlobe. Sam was letting out little breathy moans and pants. Her ears have always been a sensitive area.

Dean licked around the shell of her ear and whispered. "You drive me so crazy. Dressed like this, you drive me even crazier. Want you to dress like this all the time, be my girl. Would you like that?"

Sam gasped at the words her brother was saying to her. "You really want me to be a girl, permanently? I won't have to hide anymore?"

Dean shook his head against hers. "You'll never have to hide again." he slid his hands up into her hair and pulled.

Sam moaned at this. "Mm, love getting my hair pulled." she thrusted her hips up into his. "Dean, touch me, please."

Dean nodded and nibbled at her ear one last time before he pulled away. He climbed off the bed and pulled off her leather boots and then pulled off the fish net stockings, one by one. He removed her leather jacket and t-shirt. He removed her tank top and about blew his load as he saw her wearing the black and purple bra he found that morning.

Dean growled. "This is my favorite. It looks good on you." Sam looked away from him. Dean brought his thumb and forefinger up and lifted her chin. "Hey, you don't need to hide from me. It's just us, together, forever."

Sam looked into his eyes and nodded. Dean nodded back and brought his hands up to her skirt. He unhooked the button and pulled down the zipper. She hissed as the zipper was pulled slowly over her straining erection. Dean put his hands on either side of the skirt and pulled it down and off her legs.

Sam was now left in her underwear and Dean had to press the heel of his hand against the tent in his jeans to keep from coming at that sight alone. She was wearing a black and purple thong and the bra. Dean made quick work of removing his t-shirt and jeans so he was only in his boxers.

He crawled back on to the bed and removed her bra and the fake breasts. He laid down on top of her and started kissing her again. Sam wrapped her legs around his waist and bucked her hips up into his, slowly and sensuously.

Dean moaned into the kiss and ground down into her hips. Sam pulled away and moaned. Dean reached down in between them and cupped her erection through her panties. She gasped and bucked up into the heat that was covering her crotch.

Dean smirked and started to lightly rub her through the fabric, watching her fall apart. Sam was gasping and moaning, clutching at the sheets, and bucking her hips up into Dean's touch to get more friction. Her breath was coming out in breathy moans. "Dean! Please, more, I need more!"

Dean kept up his light stroking as he lent down to her chest and started sucking on her nipples. She made this keening noise and arched up into his mouth. She brought her hands up and ran them through his short spiky hair. Dean moaned and sucked harder, biting the nub and pulling.

She gasped again and started begging. "Dean, please, please, please, do something. Touch me, please, Dean, fuck me."

At those words, Dean stopped all his ministrations and looked up into her beautiful hazel eyes. "Sammy, are you sure about this? Are you sure you want to cross that line?"

Sam huffed at him. "Dean, we've crossed so many lines right now. C'mon, please? I really need it." she sat up and pulled her legs up and underneath her so she was kneeling on her knees. She moved forward so that she was straddling her brothers' thighs.

She looped her arms around her brother's neck and nudged her nose under his jaw. She licked a stripe up his jaw to his ear. "C'mon big brother, don't you want to know what my tight little ass feels like?" she ground down on Dean's cock and moaned dirtily in her brother's ear.

Dean grabbed on to her hair tightly and pulled it back, exposing the flesh there. He started sucking and biting at her pulse point, marking her as his. She started bucking and moaning, exposing her neck more for him.

Dean pulled away from her sweet tasting skin and whispered in her ear. "Lie down on the bed for me baby girl."

She shivered at the endearment and lay back on to the bed. Dean saw the shiver and smirked. "You like that? You like being called baby _girl_?" She moaned and arched her neck and writhed on the bed.

Dean chuckled against her skin and it sent more shivers down her spine. He skimmed his fingers lightly over her ribs and down to her waist. He took hold of the thong straps and eased them down her legs and dropped them on the floor. Dean stripped away his boxers and climbed back up on to the bed.

Sam spread her legs open so Dean could lie in between them. He slotted his hips up against hers and leaned up to kiss her. They both got lost in the kiss when Dean pulled away slightly and whispered against her lips. "I've never done this before baby girl."

Sam kissed him softly. "It's alright; I've already prepped myself. All you have to do is slick up your cock and put it in me." she reached over to the nightstand and pulled out a small bottle of lube and placed it in her brother's hand.

Dean looked at it and hesitated. Sam looked at her brother and didn't know how to interpret the look on his face. "Dean? Do you not want this? Are we going too fast?" she looked away from her brother, suddenly feeling very insecure. She tried to move away, but Dean held on to her hip, keeping her in place.

He kissed her softly. "I do want this. I- just give me a moment."

She shook her head and laid back on the bed. Dean popped the cap open and slicked some over his erect member. Sam spread her legs wider and Dean guided himself to her opening and started to ease inside her slowly.

She gasped and moaned at the feeling of her big brother's dick spreading her wide open. Dean was in a world of ecstasy, the tight, hot feeling surrounding him was amazing! Dean finally bottomed out and rested there for a moment, letting Sam get used to his girth.

Sam moaned at the feeling of fullness inside of her. She pulled on her brother's head and kissed him. "Dean, I've never felt this full before. You can move now, please move."

Dean started kissing her again as he pulled his hips out and slammed back in. Sam pulled away from the kiss and arched her head back, exposing her neck.

Dean took advantage and started sucking bruises on to her neck and kept thrusting in and out, ever so slowly. Sam was starting to get frustrated. "Just fuck me already! Please, big brother? I can take it. I like it rough."

Dean growled low in his throat. "Is that so _baby sister_?"

She gasp/moaned at Dean calling her baby sister. "_Yes_! Please, harder, faster, _please_ big brother." Dean gave her one last kiss before he started to pound her ass mercilessly.

The only sounds heard in the room were their breathless moans, gasps, and the sound of skin slapping against skin. Sam managed to sit up and push Dean down on to the bed and started riding him for all she was worth.

Dean let her ride him for a few more minutes before he turned them over so he was back on top. Dean grabbed her hips and squeezed them tightly, making sure they would bruise in the morning. Sam moaned and wrapped her legs around her brother's waist, pulling him in deeper.

Dean angled his hips just right and Sam was arching up off the bed, a silent scream escaping her mouth. Dean smirked at her and kept hitting that spot, listening to her scream his name, over and over again.

Dean was just a few short thrusts away from blowing his load. "Baby girl, I'm almost there."

Sam gasped and pulled her brother into a kiss. "Me too! Oh God, don't stop!"

Dean kept impaling on her prostate and she came, untouched, screaming her brothers' name. Dean grunted at the tightness surrounding him and gave a few more thrusts before he was coming deep inside her. He slumped forward on top of her, panting into her neck, trying to come down from his orgasmic high.

Sam was lying limp beneath her brother, panting. When she finally got her breathing under control, she turned and whispered in her brother's ear. "Damn, that was the best orgasm I have ever had."

Dean picked his head up and looked down at her and smirked. "Of course it was. You just had sex with Dean fucking Winchester."

Sam chuckled and looked at him seriously. "Did you mean it when you said you wanted me to dress like this all the time?"

Dean looked at her. "Do you not want to? I think it's kind of hot when you're all dressed up like this. I get to see those long, long legs sticking out of a short, short skirt. It gets me hard every time I think about it."

Sam started to blush and looked away from her brother. "You really think I'm hot dressed like this? And yeah, I want to dress like this all the time. I was getting tired of hiding this around you. It was getting harder and harder to keep my secret."

Dean smiled at her and gave her a chaste kiss. "Well then, I'll start saving some money away to get you whatever you need baby girl." Sam smiled back at him and started kissing him. All in all, she was glad that Dean had caught her.

From now on, Samantha will be hidden no more. No more seedy bars to visit for sex anymore. No more sex in dirty alley ways. Just her and Dean, forever and always.

THE END


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